DE3336691A1 - Verfahren zur katalytischen dimerisation von acrylsaeurederivaten und verwendung der erhaltenen dimeren - Google Patents
Verfahren zur katalytischen dimerisation von acrylsaeurederivaten und verwendung der erhaltenen dimerenInfo
- Publication number
- DE3336691A1 DE3336691A1 DE3336691A DE3336691A DE3336691A1 DE 3336691 A1 DE3336691 A1 DE 3336691A1 DE 3336691 A DE3336691 A DE 3336691A DE 3336691 A DE3336691 A DE 3336691A DE 3336691 A1 DE3336691 A1 DE 3336691A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- dimers
- linear
- nickel compounds
- dimerization
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- 239000000539 dimer Substances 0.000 title claims abstract description 21
- 230000003197 catalytic effect Effects 0.000 title claims description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 title description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 150000001450 anions Chemical class 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 238000006471 dimerization reaction Methods 0.000 claims abstract description 13
- 150000002816 nickel compounds Chemical class 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003446 ligand Substances 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 4
- 150000004678 hydrides Chemical class 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 claims description 6
- 150000003003 phosphines Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- -1 hydride ions Chemical class 0.000 claims description 2
- 238000006068 polycondensation reaction Methods 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 229910000064 phosphane Inorganic materials 0.000 abstract description 4
- 150000003002 phosphanes Chemical class 0.000 abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 150000005690 diesters Chemical class 0.000 description 6
- 229910052759 nickel Inorganic materials 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- ISZWTVCVSJVEOL-UHFFFAOYSA-N 2,5-dimethylhex-1-ene Chemical compound CC(C)CCC(C)=C ISZWTVCVSJVEOL-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- HOMQMIYUSVQSHM-UHFFFAOYSA-N cycloocta-1,3-diene;nickel Chemical compound [Ni].C1CCC=CC=CC1.C1CCC=CC=CC1 HOMQMIYUSVQSHM-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 2
- PZSJYEAHAINDJI-UHFFFAOYSA-N rhodium(3+) Chemical class [Rh+3] PZSJYEAHAINDJI-UHFFFAOYSA-N 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229910018106 Ni—C Inorganic materials 0.000 description 1
- 239000005922 Phosphane Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000002815 nickel Chemical group 0.000 description 1
- 238000006464 oxidative addition reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical group [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3336691A DE3336691A1 (de) | 1983-10-08 | 1983-10-08 | Verfahren zur katalytischen dimerisation von acrylsaeurederivaten und verwendung der erhaltenen dimeren |
| US06/657,292 US4594447A (en) | 1983-10-08 | 1984-10-03 | Process for catalytic dimerization of acrylic acid derivatives |
| DE8484111940T DE3472952D1 (en) | 1983-10-08 | 1984-10-05 | Process for the catalytic dimerization of acrylic-acid derivatives and use of the dimers thus obtained |
| AT84111940T ATE35979T1 (de) | 1983-10-08 | 1984-10-05 | Verfahren zur katalytischen dimerisation von acrylsaeurederivaten und verwendung der erhaltenen dimeren. |
| EP84111940A EP0140210B1 (fr) | 1983-10-08 | 1984-10-05 | Procédé de dimérisation catalytique de dérivés d'acide acrylique et utilisation de dimères obtenus |
| CA000464911A CA1234835A (fr) | 1983-10-08 | 1984-10-05 | Dimerisation catalytique des derives d'acide acrylique, et emploi de ces dimeres |
| JP59212399A JPS6097934A (ja) | 1983-10-08 | 1984-10-08 | アクリル酸誘導体の接触二量化法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3336691A DE3336691A1 (de) | 1983-10-08 | 1983-10-08 | Verfahren zur katalytischen dimerisation von acrylsaeurederivaten und verwendung der erhaltenen dimeren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3336691A1 true DE3336691A1 (de) | 1985-04-25 |
Family
ID=6211371
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3336691A Withdrawn DE3336691A1 (de) | 1983-10-08 | 1983-10-08 | Verfahren zur katalytischen dimerisation von acrylsaeurederivaten und verwendung der erhaltenen dimeren |
| DE8484111940T Expired DE3472952D1 (en) | 1983-10-08 | 1984-10-05 | Process for the catalytic dimerization of acrylic-acid derivatives and use of the dimers thus obtained |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8484111940T Expired DE3472952D1 (en) | 1983-10-08 | 1984-10-05 | Process for the catalytic dimerization of acrylic-acid derivatives and use of the dimers thus obtained |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4594447A (fr) |
| EP (1) | EP0140210B1 (fr) |
| JP (1) | JPS6097934A (fr) |
| AT (1) | ATE35979T1 (fr) |
| CA (1) | CA1234835A (fr) |
| DE (2) | DE3336691A1 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4781868A (en) * | 1985-12-18 | 1988-11-01 | Rohm Gmbh | Method for making unsaturated aliphatic carboxylic acid anhydrides |
| US9796654B2 (en) | 2014-05-20 | 2017-10-24 | Basf Se | Process for the dimerization of activated olefins |
| US10066188B2 (en) | 2013-12-20 | 2018-09-04 | Basf Se | Aroma chemicals |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2584310A1 (fr) * | 1985-07-04 | 1987-01-09 | Centre Nat Rech Scient | Catalyseur de dimerisation selective de l'ethylene ou du propylene en mono-olefines, du type a base de nickel sur support de silice, procede de preparation et procede de dimerisation le mettant en oeuvre |
| FR2596390B1 (fr) * | 1986-03-27 | 1989-02-17 | Rhone Poulenc Chimie | Procede de (co)dimerisation catalytique d'un acrylate d'alkyle inferieur et composition catalytique |
| FR2619564B1 (fr) * | 1987-08-19 | 1989-12-08 | Rhone Poulenc Chimie | Perfectionnement au procede de dimerisation catalytique d'un acrylate d'alkyle |
| US5099048A (en) * | 1990-09-11 | 1992-03-24 | The University Of North Carolina At Chapel Hill | Rhodium-catalyzed olefin dimerization |
| US5099061A (en) * | 1990-09-11 | 1992-03-24 | The University Of North Carolina At Chapel Hill | Rhodium-catalyzed olefin dimerization |
| US5892101A (en) * | 1996-11-18 | 1999-04-06 | E. I. Du Pont De Nemours And Company | Cross-dimerization of olefins |
| DE10318697A1 (de) * | 2003-04-24 | 2004-11-25 | Basf Ag | Verfahren zur Hydrierung einer monoolefinisch ungesättigten Verbindung |
| DE10328714A1 (de) * | 2003-06-25 | 2005-01-13 | Basf Ag | Verfahren zur Abtrennung eines Rhodium enthaltenden Homogenkatalysators |
| DE10328715A1 (de) * | 2003-06-25 | 2005-01-13 | Basf Ag | Verfahren zur kontinuierlichen Herstellung einer Verbindung, die mindestens zwei funktionelle Gruppen trägt |
| DE10328713A1 (de) * | 2003-06-25 | 2005-01-20 | Basf Ag | Verfahren zur Abtrennung eines Homogenkatalysators |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2232785A (en) * | 1938-12-20 | 1941-02-25 | Du Pont | Preparation of low molecular weight polymers of vinylidene compounds |
| US3074999A (en) * | 1958-12-31 | 1963-01-22 | American Cyanamid Co | Preparation of dialkyl 2-methyleneglutarates |
| US3013066A (en) * | 1961-03-23 | 1961-12-12 | Du Pont | Dimerization of alpha olefins with a group viii noble metal salt |
| US3417130A (en) * | 1964-06-24 | 1968-12-17 | Union Carbide Corp | Oligomerization |
| FR2005790A1 (en) * | 1968-04-08 | 1969-12-19 | Toa Gosei Chemical Indus | But-1-ene-2,3,4-tricarboxylic ester is prepared by reacting acrylic ester with maleic or fumaric ester in presence of phosphine-type catalyst. New cpds. a |
| US3853961A (en) * | 1969-08-19 | 1974-12-10 | Bayer Ag | Process for the production of dicarboxylic acid esters and the corresponding dicarboxylic acids |
| DE2104626C2 (de) * | 1970-02-09 | 1982-07-29 | Mitsubishi Chemical Industries, Ltd., Tokyo | Verfahren zur Herstellung eines Additionsproduktes eines konjugierten Diens und einer Verbindung mit endständiger Venylgruppe |
| JPS4911215A (fr) * | 1972-05-30 | 1974-01-31 | ||
| US4144257A (en) * | 1974-10-17 | 1979-03-13 | Takasago Perfumery Co., Ltd. | Process for preparing derivatives of conjugated diene dimers |
| FR2524341A1 (fr) * | 1982-03-31 | 1983-10-07 | Centre Nat Rech Scient | Catalyseur de dimerisation et/ou de codimerisation de derives acryliques |
| US4451665A (en) * | 1982-12-30 | 1984-05-29 | E. I. Du Pont De Nemours And Company | Process for dimerizing acrylates and methacrylates |
-
1983
- 1983-10-08 DE DE3336691A patent/DE3336691A1/de not_active Withdrawn
-
1984
- 1984-10-03 US US06/657,292 patent/US4594447A/en not_active Expired - Fee Related
- 1984-10-05 DE DE8484111940T patent/DE3472952D1/de not_active Expired
- 1984-10-05 CA CA000464911A patent/CA1234835A/fr not_active Expired
- 1984-10-05 AT AT84111940T patent/ATE35979T1/de active
- 1984-10-05 EP EP84111940A patent/EP0140210B1/fr not_active Expired
- 1984-10-08 JP JP59212399A patent/JPS6097934A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4781868A (en) * | 1985-12-18 | 1988-11-01 | Rohm Gmbh | Method for making unsaturated aliphatic carboxylic acid anhydrides |
| US10066188B2 (en) | 2013-12-20 | 2018-09-04 | Basf Se | Aroma chemicals |
| US9796654B2 (en) | 2014-05-20 | 2017-10-24 | Basf Se | Process for the dimerization of activated olefins |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1234835A (fr) | 1988-04-05 |
| US4594447A (en) | 1986-06-10 |
| EP0140210A2 (fr) | 1985-05-08 |
| EP0140210B1 (fr) | 1988-07-27 |
| DE3472952D1 (en) | 1988-09-01 |
| JPH0579659B2 (fr) | 1993-11-04 |
| ATE35979T1 (de) | 1988-08-15 |
| JPS6097934A (ja) | 1985-05-31 |
| EP0140210A3 (en) | 1987-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |